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It's very early in his adventures and he's been gotten a little bit scorn from he dwarves who were not too impressed with him and only took him on because of Gandalf. He attempts to steal from the trolls at least in part to prove to them that he has some talents and deserves some respect.

In addition, Bilbo is also probably motivated by a latent, long dormant, thirst for adventure in and of itself, something Tolkien often attributes to his Tookish ancestry.

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12y ago

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More answers

He thought that the dwarves would be disappointed in him if he returned empty-handed to them, without any food or anything, and will not respect him as a burglar of the group.

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12y ago
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He feels that if he's going to be a burglar, picking a troll's pocket is the best place to start.

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11y ago
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He wanted to prove he was a good thief. Unfortunately he pulled out a talking purse and it yelled.

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10y ago
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Yes. No. Yes. No.

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11y ago
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Q: Why does Bilbo decide to try to pick the trolls pockets?
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